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Cruises that leave from Boston sail from Flynn Cruiseport Boston, Massport's terminal at 1 Black Falcon Avenue in the South Boston Seaport, and mostly go to Bermuda or north to Canada and New England. In 2026 the season ran from April 14 to November 8: Norwegian Breakaway sailed 7-day round trips to Bermuda and Halifax almost every Sunday, Holland America ran 7- and 14-day sailings to Quebec City, Montreal and New Brunswick, and a few lines added long voyages to Iceland and one-way autumn trips to the Caribbean.
Where do cruises leave from in Boston?
All the big ships use Flynn Cruiseport Boston, also called the Black Falcon Cruise Terminal, at 1 Black Falcon Avenue, Boston, MA 02210. Holland America puts it about 2.8 miles from Logan Airport and warns the drive can take 45 to 60 minutes in traffic. Without a car, take the Silver Line SL2 bus from South Station; it stops at Drydock Avenue and Black Falcon Avenue, by the terminal. Massport publishes its parking and directions for passengers who drive.
Check whether your ship starts in Boston or only calls there. The Massport cruise schedule lists both, and most September and October dates are port calls by ships on longer itineraries, such as Cunard's Queen Mary 2 on September 29, 2026. You cannot board those in Boston.
Bermuda cruises from Boston
Norwegian Cruise Line is the main Bermuda option. In 2026 the Norwegian Breakaway sailed 7-day round trips from Boston on Sundays from April 19 to November 1, most of them calling at both Halifax and Bermuda; from late August to mid-October the Sunday sailings went to Halifax only. The season opened with a 5-day Bermuda round trip on April 14, and the ship left Boston for San Juan on November 8.
Canada and New England cruises from Boston
This is the largest group of departures, and it runs all season. Holland America's Zuiderdam alternated 7-day one-way sailings to Quebec City with 14-day round trips that return to Boston, and ran 7-day round trips to New Brunswick in July and October; the Volendam made the same New Brunswick trip in August and sailed to Montreal, one way or round trip, from July to September. In autumn, Princess (Sapphire Princess) ran 10-day one-way sailings to Quebec City on September 3, September 23 and October 13; Celebrity Silhouette made a 12-day round trip to Charlottetown on September 5; Windstar's Star Pride and Crystal Symphony left for Montreal on September 14 and October 9.
One-way sailings to Quebec City or Montreal mean a flight or train home from Canada, so price the return before you book. A round trip that ends back at Black Falcon Avenue is simpler if you are driving.
Longer voyages: Iceland and transatlantic routes
A few departures go much further. In 2026 Holland America's Volendam made a 28-day round trip from Boston to Iceland on June 20, and the Zuiderdam left on July 18 for a 35-day round trip listed as Vikings Solar Eclipse.
Can you cruise to the Caribbean or the Bahamas from Boston?
Only one way, at the end of the season, and the 2026 schedule listed no Bahamas sailings at all. The Caribbean departures were repositioning trips: Celebrity Silhouette's 10-day sailing to Fort Lauderdale and Windstar's 8-day sailing to San Juan, both on October 20, and the Norwegian Breakaway's 7-day sailing to San Juan on November 8.
When is the cruise season in Boston?
Departures start in mid-April and finish in early November. Bermuda and Canada trips run all season; September and October add the most ships, many of them on fall foliage itineraries that call at Boston. Massport had not yet posted 2027 departures when we checked on October 1, 2026, so confirm dates with the cruise line before planning a pre-cruise stay.
Before you sail
A night in town before boarding takes the pressure off a delayed flight. Our guides to things to do near the Boston cruise port and attractions near the cruise terminal cover the Seaport, and our guide to Boston on the water covers harbor trips if you want a shorter taste of the sea first. The Institute of Contemporary Art and Harpoon Brewery are also in the Seaport. For an evening on the water, see our guide to Boston harbor dinner, lunch, brunch and sunset cruises. For a hotel near the terminal, see Seaport hotels on Expedia.